Herbicidal bisazinyl compounds

Abstract

Herbicidal bisazinyl compounds of the formula ##STR1## in which A 1 and A 2 are identical or different and represent nitrogen or a C--X group, X representing hydrogen, halogen, alkyl or alkoxy, and Q 1 and Q 2 are identical or different and represent oxygen, sulphur, NH or N-alkyl, (the substituents R, X 1 , X 2 , Y 1 , Y 2 and Z representing a variety of organic radicals). The compounds of the formulas ##STR2## are also new.

What is claimed is: 
     
       1. A bisazinyl compound of the formula ##STR60## in which A 1  and A 2  are identical or different and represent nitrogen or a C--X group, X representing hydrogen, halogen, alkyl or alkoxy, Q 1  and Q 2  are identical or different and represent oxygen, sulphur, NH or N-alkyl,   R represents hydrogen, amino, hydroxyl, cyano, nitro, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino,   X 1 , X 2 , Y 1  and Y 2  are identical or different and represent hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, alkylamino, dialkylamino or optionally substituted phenoxy, and   Z represents one of the groups below: ##STR61##  where R 1  represents hydrogen, optionally substituted alkyl or optionally substituted phenyl,   R 2  represents hydrogen, hydroxyl or amino, or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkoxycarbonylalkoxy, dialkylaminocarbonylalkoxy, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, aryl, aralkyl, aryloxy, aralkyloxy, arylamino, diarylamino, aralkylamino, N-alkyl-N-arylamino, arylcarbonylamino, heteroarylamino, heteroarylcarbonylamino or arylsulphonylamino,   R 3  represents hydrogen, halogen, cyano, carboxyl, alkoxycarbonyl, alkylcarbonylamino or dialkoxyphosphoryl, and   R 4  represents formyl, cyano, carboxyl, hydroxymethyl or carbamoyl, or represents in each case optionally substituted alkoxycarbonyl, cycloalkoxycarbonyl, alkylthiocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, dialkylaminocarbonyl, alkylaminocarbonylalkoxycarbonyl, dialkylaminocarbonylalkoxycarbonyl, arylaminocarbonylalk oxycarbonyl, N-alkyl-N-arylaminocarbonylalkoxycarbonyl, pyrrolidinylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, piperazinylcarbonyl, aryloxycarbonyl, aralkyloxycarbonyl, heterocyclylalkoxycarbonyl, arylthiocarbonyl, aralkylthiocarbonyl, arylaminocarbonyl, aralkylaminocarbonyl, N-alkyl-N-arylaminocarbonyl, arylhydrazinocarbonyl, alkylhydrazinocarbonyl or phthalimidoxycarbonyl, or R 4  together with R 3  represents the group --CO--O--(CH 2 ) n  --, n representing the numbers 1 to 4.   
     
     
       2. A bisazinyl compound according to claim 1, in which A 1  and A 2  are identical or different and represent nitrogen or a C--X group, X representing hydrogen, halogen, C 1  -C 4  -alkyl or C 1  -C 4  -alkoxy,   Q 1  and Q 2  are identical or different and represent oxygen, sulphur, NH or N--C 1  -C 4  -alkyl,   R represents hydrogen, amino, hydroxyl, cyano, nitro, halogen, C 1  -C 4  -alkyl, C 1  -C 4  -halogenoalkyl, C 1  -C 4  -alkoxy, C 1  -C 4  -halogenoalkoxy, C 1  -C 4  -alkylthio, C 1  -C 4  -halogenoalkylthio, C 1  -C 4  -alkylamino, di-(C 1  -C 4  -alkyl)-amino, C 1  -C 4  -alkylcarbonylamino, C 1  -C 4  -alkoxycarbonylamino or C 1  -C 4  -alkylsulphonylamino,   X 1 , X 2 , Y 1  and Y 2  are identical or different and represent hydrogen, halogen, C 1  -C 4  -alkyl, C 1  -C 4  -halogenoalkyl, C 1  -C 4  -alkoxy, C 1  -C 4  -halogenoalkoxy, C 1  -C 4  -alkylthio, C 1  -C 4  -alkylamino or di-(C 1  -C 4  -alkyl)amino, or represents phenoxy which is optionally substituted by cyano, nitro, halogen, C 1  -C 4  -alkyl, C 1  -C 2  -halogenoalkyl, C 1  -C 4  -alkoxy, C 1  -C 2  -halogenoalkoxy, C 1  -C 4  -alkylthio, C 1  -C 2  -halogenoalkylthio and/or C 1  -C 4  -alkoxycarbonyl, and   Z represents one of the groups below ##STR62##  where R 1  represents hydrogen, or represents C 1  -C 4  -alkyl which is optionally substituted by halogen or C 1  -C 2  -alkoxy, or represents phenyl which is optionally substituted by halogen, C 1  -C 4  -alkyl and/or C 1  -C 4  -alkoxy,   R 2  represents hydrogen, hydroxyl or amino, or represents C 1  -C 6  -alkyl, C 3  -C 6  -alkenyl, C 3  -C 6  -alkinyl, C 1  -C 6  -alkoxy, C 3  -C 6  -alkenyloxy, C 1  -C 4  -alkoxycarbonyl-C 1  -C 2  -alkoxy, di-(C 1  -C 4  -alkyl)-aminocarbonyl-C 1  -C 2  -alkoxy, C 1  -C 6  -alkylamino, di-(C 1  -C 2  -alkyl)-amino, C 1  -C 6  -alkylcarbonylamino, C 1  -C 6  -alkoxycarbonylamino or C 1  -C 6  -alkylsulphonylamino, each of which is optionally substituted by halogen, or represents phenyl, phenyl-C 1  -C 4  -alkyl, phenoxy, phenyl-C 1  -C 4  -alkoxy, phenylamino, diphenylamino, phenyl-C 1  -C 4  -alkylamino, N--(C 1  -C 4  -alkyl)-N-phenylamino, pyridylamino, pyrimidylamino, pyridylcarbonylamino, phenylcarbonylamino, furylcarbonylamino, thienylcarbonylamino or phenylsulphonylamino, each of which is optionally substituted by nitro, amino, cyano, carboxyl, halogen, C 1  -C 4  -alkyl, C 1  -C 2  -halogenoalkyl, C 1  -C 4  -alkoxy, C 1  -C 2  -halogenoalkoxy, C 1  -C 4  -alkylthio, C 1  -C 2  -halogenoalkylthio, C 1  -C 4  -alkoxycarbonyl and/or di-(C 1  -C 2  -alkyl)-amino,   R 3  represents hydrogen, halogen, cyano, carboxyl, C 1  -C 6  -alkoxycarbonyl, C 1  -C 6  -alkylcarbonylamino or di-(C 1  -C 4  -alkoxy)-phosphoryl, and   R 4  represents formyl, cyano, carboxyl, hydroxymethyl or carbamoyl, or represents C 1  -C 6  -alkoxycarbonyl, C 5  -C 6  -cycloalkyloxycarbonyl, C 1  -C 6  -alkylthiocarbonyl, C 1  -C 6  -alkylaminocarbonyl or C 5  -C 6  -cycloalkylaminocarbonyl, each of which is optionally substituted by halogen, carboxyl or C 1  -C 4  -alkoxycarbonyl, or represents di-(C 1  -C 2  -alkyl)-aminocarbonyl, or represents C 1  -C 4  -alkylamino-carbonyl-C 1  -C 4  -alkoxycarbonyl, or represents di-(C 1  -C 2  -alkyl)-aminocarbonyl-C 1  -C 4  -alkoxycarbonyl, or represents phenylaminocarbonyl-C 1  -C 4  -alkoxycarbonyl, or represents methyl-N-phenylaminocarbonyl-C 1  -C 4  -alkoxycarbonyl, or represents pyrrolidinylcarbonyl, piperidinyl-carbonyl, morpholinylcarbonyl or piperazinylcarbonyl, each of which is optionally substituted by methyl and/or ethyl, or represents phenoxycarbonyl, phenyl-C 1  -C 4  -alkoxycarbonyl, furylmethoxycarbonyl, thienylmethoxycarbonyl, phenylthiocarbonyl, phenyl-C 1  -C 4  -alkylthiocarbonyl, phenylaminocarbonyl, phenyl-C 1  -C 4  -alkylamino-carbonyl, N-(C 1  -C 4  -alkyl)-N-phenylamino-carbonyl or phenylhydrazinocarbonyl or C 1  -C 4  -alkylhydrazinocarbonyl, each of which is optionally substituted by nitro, amino, cyano, carboxyl, halogen, C 1  -C 4  -alkyl, C 1  -C 2  -halogenoalkyl, C 1  -C 4  -alkoxy, C 1  -C 2  -halogenoalkoxy, C 1  -C 4  -alkylthio, C 1  -C 2  -halogenoalkylthio, C 1  -C 4  -alkoxycarbonyl and/or di-(C 1  -C 2  -alkyl)amino, or represents phthalimidoxycarbonyl, or together with R 3  represents the group --CO--O--(CH 2 ) n  --,   n representing the numbers 1 to 4, especially 2 or 3.   
     
     
       3. A compound according to claim 1, wherein such compound is 2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzaldehyde of the formula ##STR63## 
     
     
       4. A compound according to claim 1, wherein such compound is 2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzaldehyde 4-(chloro-phenylhydrazone) of the formula ##STR64## 
     
     
       5. A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1 and a diluent. 
     
     
       6. A method of combating unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound according to claim 1. 
     
     
       7. The method according to claim 6, wherein such compound is 2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzaldehyde, or   2,6-bis-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzaldehyde 4-(chloro-phenylhydrazone).   
     
     
       8. A hydroxy compound of the formula (II) ##STR65## in which A 1  and A 2  are identical or different and represent nitrogen or a C--X group, X representing hydrogen, halogen, alkyl or alkoxy, Q 1  and Q 2  are identical or different and represent oxygen, sulphur, NH or N-alkyl,   R represents hydrogen, amino, hydroxyl, cyano, nitro, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino,   X 1 , X 2 , Y 1  and Y 2  are identical or different and represent hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, alkylamino or dialkylamino, or represent optionally substituted phenoxy, and   R 1  represents hydrogen, or represents optionally substituted alkyl, or represents optionally substituted phenyl.   
     
     
       9. A halogenoalkyl compound of the formula ##STR66## in which A 1  and A 2  are identical or different and represent nitrogen or a C--X group, X representing hydrogen, halogen, alkyl or alkoxy, Q 1  and Q 2  are identical or different and represent oxygen, sulphur, NH or N-alkyl,   R represents hydrogen, amino, hydroxyl, cyano, nitro, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonylamino or alkylsulphonylamino,   X 1 , X 2 , Y 1  and Y 2  are identical or different and represent hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, alkylamino or dialkylamino, or represent optionally substituted phenoxy,   R 1  represents hydrogen, or represents optionally substituted alkyl, or represents optionally substituted phenyl, and   X 3  represents chlorine or bromine.